# Electronic Supplementary Material (ESI) for CrystEngComm.
# This journal is © The Royal Society of Chemistry 2019

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_shi_3449_fldu
_database_code_depnum_ccdc_archive 'CCDC 1939541'
loop_
_audit_author_name
_audit_author_address
'Sergiu Shova'
;Institute of Macromolecular Chemistry of the Romanian Academy
Romania
;
_audit_update_record             
;
2019-08-09 deposited with the CCDC.	2019-10-18 downloaded from the CCDC.
;
_audit_creation_date             2017-10-25
_audit_creation_method           
;
Olex2 1.2
(compiled 2017.08.10 svn.r3458 for OlexSys, GUI svn.r5381)
;
_chemical_name_common            ?
_chemical_name_systematic        
;
 ? 
;
_chemical_formula_moiety         'C16 H17 I N2 O4'
_chemical_formula_sum            'C16 H17 I N2 O4'
_chemical_formula_weight         428.22
_chemical_absolute_configuration ad
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C20 H20 N3 O2 I1'
_chemical_oxdiff_usercomment     I_138(DS_14)
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
I I -0.4742 1.8119 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 'x, y, z'
2 '-x+1/2, -y, z+1/2'
3 'x+1/2, -y+1/2, -z'
4 '-x, y+1/2, -z+1/2'

_cell_length_a                   8.1400(6)
_cell_length_b                   13.4654(5)
_cell_length_c                   16.3082(8)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     1787.52(16)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    3269
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      28.5540
_cell_measurement_theta_min      1.9600
_exptl_absorpt_coefficient_mu    1.811
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.96163
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.41 (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.591
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             848
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.15
_exptl_special_details           
;
 ? 
;
_diffrn_reflns_av_R_equivalents  0.0278
_diffrn_reflns_av_unetI/netI     0.0501
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            5637
_diffrn_reflns_theta_full        25.02
_diffrn_reflns_theta_max         25.02
_diffrn_reflns_theta_min         1.96
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 8.0797
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -46.00  78.00   1.00    3.00    --   18.10   0.00  30.00  124
  2  ω    -41.00   2.00   1.00    3.00    --   18.10 -57.00  30.00   43
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0765779000
_diffrn_orient_matrix_UB_12      0.0225052000
_diffrn_orient_matrix_UB_13      -0.0092163000
_diffrn_orient_matrix_UB_21      -0.0125615000
_diffrn_orient_matrix_UB_22      -0.0348053000
_diffrn_orient_matrix_UB_23      -0.0320480000
_diffrn_orient_matrix_UB_31      -0.0395777000
_diffrn_orient_matrix_UB_32      -0.0325029000
_diffrn_orient_matrix_UB_33      0.0279353000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_diffrn_standards_decay_%        ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_number         ?
_reflns_number_gt                2899
_reflns_number_total             3139
_reflns_odcompleteness_completeness 99.91
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_reflns_threshold_expression     >2sigma(I)
_computing_cell_refinement       'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.312
_refine_diff_density_min         -0.900
_refine_diff_density_rms         0.078
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.01(3)
_refine_ls_extinction_coef       ?
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.048
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     212
_refine_ls_number_reflns         3139
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0407
_refine_ls_R_factor_gt           0.0364
_refine_ls_restrained_S_all      1.048
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0332P)²+0.2410P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0757
_refine_ls_wR_factor_ref         0.0781
_refine_special_details          
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C7(H7)
2.b Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C4(H4), C5(H5)
2.c Idealised Me refined as rotating group:
 C8(H8A,H8B,H8C), C9(H9A,H9B,H9C), C14(H14A,H14B,H14C), C16(H16A,H16B,H16C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_calc_flag
_atom_site_disorder_assembly
_atom_site_disorder_group
_atom_site_refinement_flags_posn
I1 I -0.03676(4) 0.236202(19) 0.253447(18) 0.03823(12) Uani 1 d . . .
O1 O -0.2997(6) 0.1948(4) 0.0758(3) 0.104(2) Uani 1 d . . .
O2 O -0.1138(5) 0.1485(3) -0.0112(2) 0.0599(12) Uani 1 d . . .
O3 O -0.2105(6) -0.0697(3) -0.0109(2) 0.0674(13) Uani 1 d . . .
O4 O -0.0355(6) -0.1767(3) 0.0429(2) 0.0600(11) Uani 1 d . . .
N1 N 0.0235(5) 0.0182(3) 0.2257(2) 0.0302(9) Uani 1 d . . .
N2 N 0.0075(5) -0.0604(3) 0.1742(2) 0.0306(10) Uani 1 d . . .
C1 C 0.1025(6) 0.0045(3) 0.3038(3) 0.0294(11) Uani 1 d . . .
C2 C 0.0018(6) -0.0069(3) 0.3713(3) 0.0390(16) Uani 1 d . . .
H2 H -0.1118 -0.0030 0.3662 0.047 Uiso 1 calc . . R
C3 C 0.0744(7) -0.0246(4) 0.4471(3) 0.0459(14) Uani 1 d . . .
H3 H 0.0098 -0.0334 0.4935 0.055 Uiso 1 calc . . R
C4 C 0.2418(8) -0.0288(4) 0.4525(3) 0.0494(15) Uani 1 d . . .
H4 H 0.2909 -0.0407 0.5031 0.059 Uiso 1 calc . . R
C5 C 0.3378(7) -0.0159(4) 0.3849(3) 0.0513(16) Uani 1 d . . .
H5 H 0.4513 -0.0195 0.3905 0.062 Uiso 1 calc . . R
C6 C 0.2711(6) 0.0028(4) 0.3073(3) 0.0387(13) Uani 1 d . . .
C7 C 0.3798(7) 0.0214(5) 0.2332(3) 0.0623(17) Uani 1 d . . .
H7 H 0.3077 0.0385 0.1871 0.075 Uiso 1 calc . . R
C8 C 0.4918(9) 0.1101(6) 0.2485(5) 0.106(3) Uani 1 d . . .
H8A H 0.4269 0.1661 0.2651 0.159 Uiso 1 calc . . GR
H8B H 0.5500 0.1260 0.1990 0.159 Uiso 1 calc . . GR
H8C H 0.5690 0.0940 0.2910 0.159 Uiso 1 calc . . GR
C9 C 0.4771(11) -0.0692(7) 0.2084(5) 0.120(3) Uani 1 d . . .
H9A H 0.5384 -0.0550 0.1595 0.180 Uiso 1 calc . . GR
H9B H 0.4034 -0.1235 0.1982 0.180 Uiso 1 calc . . GR
H9C H 0.5514 -0.0868 0.2517 0.180 Uiso 1 calc . . GR
C10 C -0.0452(6) 0.1016(3) 0.1937(3) 0.0276(10) Uani 1 d . . .
C11 C -0.1027(6) 0.0767(3) 0.1171(2) 0.0252(10) Uani 1 d . . .
C12 C -0.0683(6) -0.0252(3) 0.1084(3) 0.0234(11) Uani 1 d . . .
C13 C -0.1857(6) 0.1455(4) 0.0592(3) 0.0349(12) Uani 1 d . . .
C14 C -0.1831(9) 0.2150(5) -0.0723(3) 0.070(2) Uani 1 d . . .
H14A H -0.1154 0.2145 -0.1205 0.105 Uiso 1 calc . . GR
H14B H -0.1877 0.2812 -0.0505 0.105 Uiso 1 calc . . GR
H14C H -0.2919 0.1934 -0.0862 0.105 Uiso 1 calc . . GR
C15 C -0.1150(7) -0.0920(4) 0.0402(3) 0.0380(12) Uani 1 d . . .
C16 C -0.0776(12) -0.2492(4) -0.0182(4) 0.095(3) Uani 1 d . . .
H16A H -0.0386 -0.2274 -0.0707 0.143 Uiso 1 calc . . GR
H16B H -0.1948 -0.2569 -0.0201 0.143 Uiso 1 calc . . GR
H16C H -0.0277 -0.3116 -0.0045 0.143 Uiso 1 calc . . GR


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes) 
 are estimated using the full covariance matrix.  The cell esds are taken 
 into account individually in the estimation of esds in distances, angles 
 and torsion angles; correlations between esds in cell parameters are only 
 used when they are defined by crystal symmetry.  An approximate (isotropic) 
 treatment of cell esds is used for estimating esds involving l.s. planes. 
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
I1 C10 2.059(4) . ?
O1 C13 1.172(6) . ?
O2 C13 1.290(6) . ?
O2 C14 1.454(6) . ?
O3 C15 1.179(6) . ?
O4 C15 1.313(6) . ?
O4 C16 1.436(6) . ?
N1 N2 1.358(5) . ?
N1 C1 1.438(6) . ?
N1 C10 1.358(5) . ?
N2 C12 1.324(5) . ?
C1 C2 1.381(7) . ?
C1 C6 1.374(7) . ?
C2 H2 0.9300 . ?
C2 C3 1.390(7) . ?
C3 H3 0.9300 . ?
C3 C4 1.367(8) . ?
C4 H4 0.9300 . ?
C4 C5 1.363(8) . ?
C5 H5 0.9300 . ?
C5 C6 1.399(7) . ?
C6 C7 1.519(7) . ?
C7 H7 0.9800 . ?
C7 C8 1.523(9) . ?
C7 C9 1.509(9) . ?
C8 H8A 0.9600 . ?
C8 H8B 0.9600 . ?
C8 H8C 0.9600 . ?
C9 H9A 0.9600 . ?
C9 H9B 0.9600 . ?
C9 H9C 0.9600 . ?
C10 C11 1.376(6) . ?
C11 C12 1.407(6) . ?
C11 C13 1.485(6) . ?
C12 C15 1.480(6) . ?
C14 H14A 0.9600 . ?
C14 H14B 0.9600 . ?
C14 H14C 0.9600 . ?
C16 H16A 0.9600 . ?
C16 H16B 0.9600 . ?
C16 H16C 0.9600 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C13 O2 C14 116.9(5) . . ?
C15 O4 C16 116.7(4) . . ?
N2 N1 C1 119.4(3) . . ?
C10 N1 N2 111.5(4) . . ?
C10 N1 C1 129.1(4) . . ?
C12 N2 N1 105.5(3) . . ?
C2 C1 N1 117.1(4) . . ?
C6 C1 N1 119.1(4) . . ?
C6 C1 C2 123.9(5) . . ?
C1 C2 H2 120.8 . . ?
C1 C2 C3 118.4(5) . . ?
C3 C2 H2 120.8 . . ?
C2 C3 H3 120.4 . . ?
C4 C3 C2 119.3(5) . . ?
C4 C3 H3 120.4 . . ?
C3 C4 H4 119.6 . . ?
C5 C4 C3 120.9(5) . . ?
C5 C4 H4 119.6 . . ?
C4 C5 H5 118.9 . . ?
C4 C5 C6 122.2(5) . . ?
C6 C5 H5 118.9 . . ?
C1 C6 C5 115.4(5) . . ?
C1 C6 C7 123.1(5) . . ?
C5 C6 C7 121.6(5) . . ?
C6 C7 H7 107.4 . . ?
C8 C7 C6 110.3(5) . . ?
C8 C7 H7 107.4 . . ?
C9 C7 C6 112.7(6) . . ?
C9 C7 H7 107.4 . . ?
C9 C7 C8 111.3(6) . . ?
C7 C8 H8A 109.5 . . ?
C7 C8 H8B 109.5 . . ?
C7 C8 H8C 109.5 . . ?
H8A C8 H8B 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
C7 C9 H9A 109.5 . . ?
C7 C9 H9B 109.5 . . ?
C7 C9 H9C 109.5 . . ?
H9A C9 H9B 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
N1 C10 I1 122.2(3) . . ?
N1 C10 C11 106.7(4) . . ?
C11 C10 I1 130.9(3) . . ?
C10 C11 C12 105.1(4) . . ?
C10 C11 C13 125.5(4) . . ?
C12 C11 C13 129.4(4) . . ?
N2 C12 C11 111.1(4) . . ?
N2 C12 C15 120.7(4) . . ?
C11 C12 C15 128.0(4) . . ?
O1 C13 O2 123.2(5) . . ?
O1 C13 C11 124.5(5) . . ?
O2 C13 C11 112.2(4) . . ?
O2 C14 H14A 109.5 . . ?
O2 C14 H14B 109.5 . . ?
O2 C14 H14C 109.5 . . ?
H14A C14 H14B 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
O3 C15 O4 124.8(5) . . ?
O3 C15 C12 123.1(5) . . ?
O4 C15 C12 112.1(4) . . ?
O4 C16 H16A 109.5 . . ?
O4 C16 H16B 109.5 . . ?
O4 C16 H16C 109.5 . . ?
H16A C16 H16B 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
I1 C10 C11 C12 177.0(4) . . . . ?
I1 C10 C11 C13 -4.2(8) . . . . ?
N1 N2 C12 C11 -0.3(5) . . . . ?
N1 N2 C12 C15 -176.7(4) . . . . ?
N1 C1 C2 C3 177.3(4) . . . . ?
N1 C1 C6 C5 -176.9(4) . . . . ?
N1 C1 C6 C7 4.0(8) . . . . ?
N1 C10 C11 C12 1.9(5) . . . . ?
N1 C10 C11 C13 -179.2(5) . . . . ?
N2 N1 C1 C2 -99.3(5) . . . . ?
N2 N1 C1 C6 80.2(6) . . . . ?
N2 N1 C10 I1 -177.9(3) . . . . ?
N2 N1 C10 C11 -2.3(6) . . . . ?
N2 C12 C15 O3 163.8(5) . . . . ?
N2 C12 C15 O4 -17.5(7) . . . . ?
C1 N1 N2 C12 -179.9(4) . . . . ?
C1 N1 C10 I1 3.8(7) . . . . ?
C1 N1 C10 C11 179.4(5) . . . . ?
C1 C2 C3 C4 0.8(8) . . . . ?
C1 C6 C7 C8 120.8(6) . . . . ?
C1 C6 C7 C9 -114.1(7) . . . . ?
C2 C1 C6 C5 2.6(8) . . . . ?
C2 C1 C6 C7 -176.4(5) . . . . ?
C2 C3 C4 C5 0.1(9) . . . . ?
C3 C4 C5 C6 0.4(10) . . . . ?
C4 C5 C6 C1 -1.6(9) . . . . ?
C4 C5 C6 C7 177.4(5) . . . . ?
C5 C6 C7 C8 -58.2(8) . . . . ?
C5 C6 C7 C9 66.9(8) . . . . ?
C6 C1 C2 C3 -2.2(8) . . . . ?
C10 N1 N2 C12 1.6(5) . . . . ?
C10 N1 C1 C2 78.9(6) . . . . ?
C10 N1 C1 C6 -101.5(6) . . . . ?
C10 C11 C12 N2 -1.0(6) . . . . ?
C10 C11 C12 C15 175.0(5) . . . . ?
C10 C11 C13 O1 -52.7(8) . . . . ?
C10 C11 C13 O2 124.6(5) . . . . ?
C11 C12 C15 O3 -11.9(9) . . . . ?
C11 C12 C15 O4 166.8(5) . . . . ?
C12 C11 C13 O1 125.8(7) . . . . ?
C12 C11 C13 O2 -56.9(7) . . . . ?
C13 C11 C12 N2 -179.8(5) . . . . ?
C13 C11 C12 C15 -3.7(9) . . . . ?
C14 O2 C13 O1 -1.6(9) . . . . ?
C14 O2 C13 C11 -178.9(5) . . . . ?
C16 O4 C15 O3 -4.3(9) . . . . ?
C16 O4 C15 C12 176.9(5) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.040
_oxdiff_exptl_absorpt_empirical_full_min 0.969
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_shi_3466_fldu
_database_code_depnum_ccdc_archive 'CCDC 1939543'
loop_
_audit_author_name
_audit_author_address
'Sergiu Shova'
;Institute of Macromolecular Chemistry of the Romanian Academy
Romania
;
_audit_update_record             
;
2019-08-09 deposited with the CCDC.	2019-10-18 downloaded from the CCDC.
;
_audit_creation_date             2017-10-25
_audit_creation_method           
;
Olex2 1.2
(compiled 2017.08.10 svn.r3458 for OlexSys, GUI svn.r5381)
;
_chemical_name_common            ?
_chemical_name_systematic        
;
 ? 
;
_chemical_formula_moiety         'C14 H12 Cl I N2 O4'
_chemical_formula_sum            'C14 H12 Cl I N2 O4'
_chemical_formula_weight         434.61
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C20 H20 N4 O2'
_chemical_oxdiff_usercomment     D_26
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
I I -0.4742 1.8119 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 'x, y, z'
2 '-x, -y, -z'

_cell_length_a                   8.3915(7)
_cell_length_b                   10.0389(8)
_cell_length_c                   10.2106(9)
_cell_angle_alpha                111.275(8)
_cell_angle_beta                 96.662(7)
_cell_angle_gamma                95.904(7)
_cell_volume                     786.30(11)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    2582
_cell_measurement_temperature    200.00(10)
_cell_measurement_theta_max      25.4880
_cell_measurement_theta_min      2.1640
_exptl_absorpt_coefficient_mu    2.225
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.83953
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.41 (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.836
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             424
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.25
_exptl_special_details           
;
 ? 
;
_diffrn_reflns_av_R_equivalents  0.0340
_diffrn_reflns_av_unetI/netI     0.0473
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            7393
_diffrn_reflns_theta_full        25.03
_diffrn_reflns_theta_max         25.03
_diffrn_reflns_theta_min         2.17
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      200.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.1593
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω      3.00  83.00   1.00    7.00    --   17.87  38.00  60.00   80
  2  ω      3.00  68.00   1.00    7.00    --   17.87  57.00  90.00   65
  3  ω     -9.00  85.00   1.00    7.00    --   17.87  77.00 -90.00   94
  4  ω    -50.00  45.00   1.00    7.00    --   17.87 -77.00 150.00   95
  5  ω    -60.00 -35.00   1.00    7.00    --  -15.52-178.00 120.00   25
  6  ω    -78.00   1.00   1.00    7.00    --  -15.29 -57.00 150.00   79
  7  ω    -24.00  57.00   1.00    7.00    --   17.71 -99.00  60.00   81
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0519668000
_diffrn_orient_matrix_UB_12      -0.0059154000
_diffrn_orient_matrix_UB_13      0.0483323000
_diffrn_orient_matrix_UB_21      -0.0576344000
_diffrn_orient_matrix_UB_22      0.0324072000
_diffrn_orient_matrix_UB_23      -0.0298947000
_diffrn_orient_matrix_UB_31      -0.0374418000
_diffrn_orient_matrix_UB_32      -0.0693423000
_diffrn_orient_matrix_UB_33      -0.0498397000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_diffrn_standards_decay_%        ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_number         ?
_reflns_number_gt                2427
_reflns_number_total             2768
_reflns_odcompleteness_completeness 99.94
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_reflns_threshold_expression     >2sigma(I)
_computing_cell_refinement       'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         2.304
_refine_diff_density_min         -0.816
_refine_diff_density_rms         0.133
_refine_ls_extinction_coef       ?
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.053
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     202
_refine_ls_number_reflns         2768
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0574
_refine_ls_R_factor_gt           0.0490
_refine_ls_restrained_S_all      1.053
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0763P)²+1.3028P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1281
_refine_ls_wR_factor_ref         0.1351
_refine_special_details          
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C2(H2), C4(H4), C3(H3)
2.b Idealised Me refined as rotating group:
 C14(H14A,H14B,H14C), C7(H7A,H7B,H7C), C12(H12A,H12B,H12C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_calc_flag
_atom_site_disorder_assembly
_atom_site_disorder_group
_atom_site_refinement_flags_posn
I1 I 0.72294(5) 0.41210(5) 0.43738(4) 0.0423(2) Uani 1 d . . .
Cl1 Cl 1.0545(2) 0.8250(2) 1.0061(2) 0.0563(5) Uani 1 d . . .
O2 O 0.2190(5) 0.1841(5) 0.4727(4) 0.0373(10) Uani 1 d . . .
O3 O 0.2932(5) 0.0034(5) 0.6265(5) 0.0397(10) Uani 1 d . . .
O4 O 0.4251(5) 0.1192(5) 0.8523(4) 0.0384(10) Uani 1 d . . .
O1 O 0.3827(5) 0.1481(6) 0.3080(4) 0.0469(12) Uani 1 d . . .
N1 N 0.7324(6) 0.3281(6) 0.6922(5) 0.0393(13) Uani 1 d . . .
N2 N 0.6515(6) 0.2552(6) 0.7609(5) 0.0374(13) Uani 1 d . . .
C13 C 0.3978(7) 0.0960(6) 0.7143(6) 0.0313(13) Uani 1 d . . .
C10 C 0.5114(7) 0.1932(7) 0.6772(6) 0.0308(13) Uani 1 d . . .
C9 C 0.4960(7) 0.2267(6) 0.5519(6) 0.0299(13) Uani 1 d . . .
C8 C 0.6396(7) 0.3128(7) 0.5659(6) 0.0342(14) Uani 1 d . . .
C11 C 0.3640(7) 0.1796(6) 0.4296(6) 0.0320(13) Uani 1 d . . .
C1 C 0.8852(7) 0.4170(7) 0.7601(6) 0.0372(15) Uani 1 d . . .
C2 C 1.0259(8) 0.3513(8) 0.7416(7) 0.0438(16) Uani 1 d . . .
H2 H 1.0194 0.2529 0.6887 0.053 Uiso 1 calc . . R
C6 C 0.8853(7) 0.5596(8) 0.8404(7) 0.0402(15) Uani 1 d . . .
C4 C 1.1808(8) 0.5829(8) 0.8887(7) 0.0422(16) Uani 1 d . . .
H4 H 1.2804 0.6404 0.9347 0.051 Uiso 1 calc . . R
C3 C 1.1773(8) 0.4407(8) 0.8065(7) 0.0447(17) Uani 1 d . . .
H3 H 1.2735 0.4029 0.7933 0.054 Uiso 1 calc . . R
C14 C 0.3287(8) 0.0171(7) 0.8922(7) 0.0433(16) Uani 1 d . . .
H14A H 0.2161 0.0106 0.8564 0.065 Uiso 1 calc . . GR
H14B H 0.3444 0.0490 0.9942 0.065 Uiso 1 calc . . GR
H14C H 0.3616 -0.0762 0.8527 0.065 Uiso 1 calc . . GR
C5 C 1.0422(9) 0.6432(7) 0.9053(7) 0.0435(16) Uani 1 d . . .
C7 C 0.7334(9) 0.6227(8) 0.8615(8) 0.0511(18) Uani 1 d . . .
H7A H 0.6417 0.5494 0.8095 0.077 Uiso 1 calc . . GR
H7B H 0.7346 0.7003 0.8277 0.077 Uiso 1 calc . . GR
H7C H 0.7258 0.6592 0.9611 0.077 Uiso 1 calc . . GR
C12 C 0.0802(8) 0.1302(9) 0.3607(8) 0.057(2) Uani 1 d . . .
H12A H 0.1019 0.0478 0.2843 0.085 Uiso 1 calc . . GR
H12B H 0.0585 0.2046 0.3260 0.085 Uiso 1 calc . . GR
H12C H -0.0126 0.1021 0.3971 0.085 Uiso 1 calc . . GR


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes) 
 are estimated using the full covariance matrix.  The cell esds are taken 
 into account individually in the estimation of esds in distances, angles 
 and torsion angles; correlations between esds in cell parameters are only 
 used when they are defined by crystal symmetry.  An approximate (isotropic) 
 treatment of cell esds is used for estimating esds involving l.s. planes. 
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
I1 C8 2.055(6) . ?
Cl1 C5 1.725(7) . ?
O2 C11 1.340(7) . ?
O2 C12 1.439(7) . ?
O3 C13 1.218(7) . ?
O4 C13 1.330(7) . ?
O4 C14 1.442(8) . ?
O1 C11 1.199(7) . ?
N1 N2 1.367(7) . ?
N1 C8 1.375(8) . ?
N1 C1 1.425(8) . ?
N2 C10 1.316(7) . ?
C13 C10 1.471(8) . ?
C10 C9 1.432(8) . ?
C9 C8 1.369(8) . ?
C9 C11 1.467(8) . ?
C1 C2 1.409(9) . ?
C1 C6 1.368(9) . ?
C2 H2 0.9300 . ?
C2 C3 1.413(10) . ?
C6 C5 1.430(9) . ?
C6 C7 1.484(9) . ?
C4 H4 0.9300 . ?
C4 C3 1.364(10) . ?
C4 C5 1.365(10) . ?
C3 H3 0.9300 . ?
C14 H14A 0.9600 . ?
C14 H14B 0.9600 . ?
C14 H14C 0.9600 . ?
C7 H7A 0.9600 . ?
C7 H7B 0.9600 . ?
C7 H7C 0.9600 . ?
C12 H12A 0.9600 . ?
C12 H12B 0.9600 . ?
C12 H12C 0.9600 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C11 O2 C12 115.5(5) . . ?
C13 O4 C14 114.8(5) . . ?
N2 N1 C8 111.0(5) . . ?
N2 N1 C1 119.9(5) . . ?
C8 N1 C1 128.8(5) . . ?
C10 N2 N1 105.5(5) . . ?
O3 C13 O4 124.5(6) . . ?
O3 C13 C10 123.0(5) . . ?
O4 C13 C10 112.5(5) . . ?
N2 C10 C13 119.9(5) . . ?
N2 C10 C9 111.7(5) . . ?
C9 C10 C13 128.3(5) . . ?
C10 C9 C11 130.4(5) . . ?
C8 C9 C10 104.4(5) . . ?
C8 C9 C11 125.1(6) . . ?
N1 C8 I1 121.2(4) . . ?
C9 C8 I1 131.4(5) . . ?
C9 C8 N1 107.4(5) . . ?
O2 C11 C9 110.8(5) . . ?
O1 C11 O2 124.2(5) . . ?
O1 C11 C9 124.8(5) . . ?
C2 C1 N1 117.7(6) . . ?
C6 C1 N1 117.8(6) . . ?
C6 C1 C2 124.4(6) . . ?
C1 C2 H2 121.3 . . ?
C1 C2 C3 117.4(7) . . ?
C3 C2 H2 121.3 . . ?
C1 C6 C5 115.2(6) . . ?
C1 C6 C7 122.5(6) . . ?
C5 C6 C7 122.2(6) . . ?
C3 C4 H4 119.1 . . ?
C3 C4 C5 121.8(7) . . ?
C5 C4 H4 119.1 . . ?
C2 C3 H3 120.4 . . ?
C4 C3 C2 119.3(7) . . ?
C4 C3 H3 120.4 . . ?
O4 C14 H14A 109.5 . . ?
O4 C14 H14B 109.5 . . ?
O4 C14 H14C 109.5 . . ?
H14A C14 H14B 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
C6 C5 Cl1 118.5(6) . . ?
C4 C5 Cl1 119.8(6) . . ?
C4 C5 C6 121.7(7) . . ?
C6 C7 H7A 109.5 . . ?
C6 C7 H7B 109.5 . . ?
C6 C7 H7C 109.5 . . ?
H7A C7 H7B 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
O2 C12 H12A 109.5 . . ?
O2 C12 H12B 109.5 . . ?
O2 C12 H12C 109.5 . . ?
H12A C12 H12B 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O3 C13 C10 N2 -157.1(6) . . . . ?
O3 C13 C10 C9 18.7(10) . . . . ?
O4 C13 C10 N2 21.6(8) . . . . ?
O4 C13 C10 C9 -162.5(6) . . . . ?
N1 N2 C10 C13 175.4(5) . . . . ?
N1 N2 C10 C9 -1.1(7) . . . . ?
N1 C1 C2 C3 178.6(6) . . . . ?
N1 C1 C6 C5 -179.8(5) . . . . ?
N1 C1 C6 C7 1.5(9) . . . . ?
N2 N1 C8 I1 178.8(4) . . . . ?
N2 N1 C8 C9 -0.6(7) . . . . ?
N2 N1 C1 C2 88.3(7) . . . . ?
N2 N1 C1 C6 -90.8(8) . . . . ?
N2 C10 C9 C8 0.7(7) . . . . ?
N2 C10 C9 C11 178.6(6) . . . . ?
C13 C10 C9 C8 -175.4(6) . . . . ?
C13 C10 C9 C11 2.5(10) . . . . ?
C10 C9 C8 I1 -179.4(5) . . . . ?
C10 C9 C8 N1 0.0(7) . . . . ?
C10 C9 C11 O2 43.0(8) . . . . ?
C10 C9 C11 O1 -140.4(7) . . . . ?
C8 N1 N2 C10 1.1(7) . . . . ?
C8 N1 C1 C2 -98.7(8) . . . . ?
C8 N1 C1 C6 82.2(8) . . . . ?
C8 C9 C11 O2 -139.5(6) . . . . ?
C8 C9 C11 O1 37.1(10) . . . . ?
C11 C9 C8 I1 2.6(9) . . . . ?
C11 C9 C8 N1 -178.1(5) . . . . ?
C1 N1 N2 C10 175.2(6) . . . . ?
C1 N1 C8 I1 5.3(9) . . . . ?
C1 N1 C8 C9 -174.1(6) . . . . ?
C1 C2 C3 C4 3.1(10) . . . . ?
C1 C6 C5 Cl1 178.9(5) . . . . ?
C1 C6 C5 C4 -0.8(9) . . . . ?
C2 C1 C6 C5 1.2(9) . . . . ?
C2 C1 C6 C7 -177.5(6) . . . . ?
C6 C1 C2 C3 -2.4(10) . . . . ?
C3 C4 C5 Cl1 -178.0(5) . . . . ?
C3 C4 C5 C6 1.6(10) . . . . ?
C14 O4 C13 O3 4.9(8) . . . . ?
C14 O4 C13 C10 -173.8(5) . . . . ?
C5 C4 C3 C2 -2.8(10) . . . . ?
C7 C6 C5 Cl1 -2.4(9) . . . . ?
C7 C6 C5 C4 177.9(6) . . . . ?
C12 O2 C11 O1 7.6(9) . . . . ?
C12 O2 C11 C9 -175.7(6) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.165
_oxdiff_exptl_absorpt_empirical_full_min 0.872
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_shi_3475_fldu
_database_code_depnum_ccdc_archive 'CCDC 1939542'
loop_
_audit_author_name
_audit_author_address
'Sergiu Shova'
;Institute of Macromolecular Chemistry of the Romanian Academy
Romania
;
_audit_update_record             
;
2019-08-09 deposited with the CCDC.	2019-10-18 downloaded from the CCDC.
;
_audit_creation_date             2017-10-25
_audit_creation_method           
;
Olex2 1.2
(compiled 2017.08.10 svn.r3458 for OlexSys, GUI svn.r5381)
;
_chemical_name_common            ?
_chemical_name_systematic        
;
 ? 
;
_chemical_formula_moiety         'C14 H13 I N2 O5'
_chemical_formula_sum            'C14 H13 I N2 O5'
_chemical_formula_weight         416.16
_chemical_absolute_configuration ad
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C20 H20 N2 O4 I1'
_chemical_oxdiff_usercomment     RT_78
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
I I -0.4742 1.8119 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           9
_space_group_name_H-M_alt        'C 1 c 1'
_space_group_name_Hall           'C -2yc'
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 'x, y, z'
2 'x, -y, z+1/2'
3 'x+1/2, y+1/2, z'
4 'x+1/2, -y+1/2, z+1/2'

_cell_length_a                   23.0873(10)
_cell_length_b                   9.6374(3)
_cell_length_c                   7.2450(3)
_cell_angle_alpha                90.00
_cell_angle_beta                 106.961(4)
_cell_angle_gamma                90.00
_cell_volume                     1541.91(10)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    5803
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      27.4440
_cell_measurement_theta_min      1.8760
_exptl_absorpt_coefficient_mu    2.102
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.73007
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.41 (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.793
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             816
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.15
_exptl_special_details           
;
 ? 
;
_diffrn_reflns_av_R_equivalents  0.0369
_diffrn_reflns_av_unetI/netI     0.0405
_diffrn_reflns_limit_h_max       27
_diffrn_reflns_limit_h_min       -27
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_number            10152
_diffrn_reflns_theta_full        25.02
_diffrn_reflns_theta_max         25.02
_diffrn_reflns_theta_min         1.84
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 8.0797
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -16.00  10.00   1.00    7.00    --  -15.60 -99.00 -30.00   26
  2  ω    -11.00  89.00   1.00    7.00    --   17.79  19.00  30.00  100
  3  ω     -3.00  77.00   1.00    7.00    --   17.79  19.00 120.00   80
  4  ω    -88.00 -43.00   1.00    7.00    --  -15.44 178.00  60.00   45
  5  ω     56.00  88.00   1.00    7.00    --   17.79 178.00 150.00   32
  6  ω    -13.00  55.00   1.00    7.00    --   17.79 -99.00 -30.00   68
  7  ω    -59.00 -33.00   1.00    7.00    --  -15.44 178.00-120.00   26
  8  ω     -4.00  23.00   1.00    7.00    --  -15.44 -99.00   0.00   27
  9  ω     16.00  57.00   1.00    7.00    --   17.79 -99.00-150.00   41
 10  ω     42.00  74.00   1.00    7.00    --   17.79  57.00 -90.00   32
 11  ω     30.00  57.00   1.00    7.00    --   17.79 -99.00  90.00   27
 12  ω    -25.00  14.00   1.00    7.00    --   17.79 -99.00  90.00   39
 13  ω      2.00  87.00   1.00    7.00    --   17.79  38.00-180.00   85
 14  ω     -9.00  84.00   1.00    7.00    --   17.79  77.00-150.00   93
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0481634000
_diffrn_orient_matrix_UB_12      0.0162035000
_diffrn_orient_matrix_UB_13      -0.0267021000
_diffrn_orient_matrix_UB_21      -0.0785325000
_diffrn_orient_matrix_UB_22      -0.0193055000
_diffrn_orient_matrix_UB_23      -0.0178175000
_diffrn_orient_matrix_UB_31      -0.0331794000
_diffrn_orient_matrix_UB_32      0.0691378000
_diffrn_orient_matrix_UB_33      0.0012816000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_diffrn_standards_decay_%        ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_number         ?
_reflns_number_gt                2623
_reflns_number_total             2731
_reflns_odcompleteness_completeness 100.00
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_reflns_threshold_expression     >2sigma(I)
_computing_cell_refinement       'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.255
_refine_diff_density_min         -0.390
_refine_diff_density_rms         0.074
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.033(15)
_refine_ls_extinction_coef       ?
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.023
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     202
_refine_ls_number_reflns         2731
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.0280
_refine_ls_R_factor_gt           0.0257
_refine_ls_restrained_S_all      1.023
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0186P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0452
_refine_ls_wR_factor_ref         0.0460
_refine_special_details          
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C4(H4), C6(H6)
2.b Idealised Me refined as rotating group:
 C7(H7A,H7B,H7C), C12(H12A,H12B,H12C), C14(H14A,H14B,H14C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_calc_flag
_atom_site_disorder_assembly
_atom_site_disorder_group
_atom_site_refinement_flags_posn
I1 I -0.25557(2) 0.384473(18) 0.33633(4) 0.03857(8) Uani 1 d . . .
O1 O -0.38892(13) 0.2266(3) 0.1801(5) 0.0513(9) Uani 1 d . . .
O2 O -0.39667(13) 0.0266(3) 0.3301(4) 0.0379(7) Uani 1 d . . .
O3 O -0.26696(16) -0.2954(2) 0.3459(7) 0.0432(11) Uani 1 d . . .
O4 O -0.35671(12) -0.2091(2) 0.1814(4) 0.0424(8) Uani 1 d . . .
O5 O -0.05967(15) 0.3231(4) 0.0594(5) 0.0582(9) Uani 1 d . . .
N1 N -0.20577(19) 0.0970(4) 0.3221(6) 0.0254(10) Uani 1 d . . .
N2 N -0.21670(15) -0.0418(3) 0.3134(5) 0.0284(8) Uani 1 d . . .
C1 C -0.1447(2) 0.1436(5) 0.3396(7) 0.0298(13) Uani 1 d . . .
C2 C -0.0988(2) 0.0996(4) 0.4962(7) 0.0466(12) Uani 1 d . . .
H2 H -0.1065 0.0468 0.5938 0.056 Uiso 1 calc . . R
C3 C -0.0401(2) 0.1377(5) 0.5021(8) 0.0552(14) Uani 1 d . . .
H3 H -0.0080 0.1120 0.6077 0.066 Uiso 1 calc . . R
C4 C -0.0287(2) 0.2116(4) 0.3569(7) 0.0474(12) Uani 1 d . . .
H4 H 0.0109 0.2347 0.3637 0.057 Uiso 1 calc . . R
C5 C -0.07551(18) 0.2528(4) 0.1993(6) 0.0367(10) Uani 1 d . . .
C6 C -0.13520(17) 0.2201(4) 0.1912(6) 0.0319(9) Uani 1 d . . .
H6 H -0.1675 0.2492 0.0885 0.038 Uiso 1 calc . . R
C7 C -0.1067(3) 0.3644(6) -0.1084(9) 0.0721(18) Uani 1 d . . .
H7A H -0.1349 0.4230 -0.0709 0.108 Uiso 1 calc . . GR
H7B H -0.1273 0.2835 -0.1727 0.108 Uiso 1 calc . . GR
H7C H -0.0894 0.4142 -0.1941 0.108 Uiso 1 calc . . GR
C8 C -0.2563(3) 0.1717(3) 0.3034(9) 0.0290(13) Uani 1 d . . .
C9 C -0.3045(2) 0.0772(5) 0.2769(6) 0.0243(11) Uani 1 d . . .
C10 C -0.27536(18) -0.0532(4) 0.2899(6) 0.0259(10) Uani 1 d . . .
C11 C -0.3670(3) 0.1200(5) 0.2559(8) 0.0322(14) Uani 1 d . . .
C12 C -0.4581(2) 0.0614(5) 0.3224(8) 0.0522(13) Uani 1 d . . .
H12A H -0.4776 -0.0185 0.3561 0.078 Uiso 1 calc . . GR
H12B H -0.4797 0.0909 0.1942 0.078 Uiso 1 calc . . GR
H12C H -0.4578 0.1351 0.4118 0.078 Uiso 1 calc . . GR
C13 C -0.29919(19) -0.1988(4) 0.2785(6) 0.0289(9) Uani 1 d . . .
C14 C -0.3831(2) -0.3454(5) 0.1743(9) 0.0578(15) Uani 1 d . . .
H14A H -0.4262 -0.3390 0.1205 0.087 Uiso 1 calc . . GR
H14B H -0.3736 -0.3829 0.3024 0.087 Uiso 1 calc . . GR
H14C H -0.3670 -0.4050 0.0951 0.087 Uiso 1 calc . . GR


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes) 
 are estimated using the full covariance matrix.  The cell esds are taken 
 into account individually in the estimation of esds in distances, angles 
 and torsion angles; correlations between esds in cell parameters are only 
 used when they are defined by crystal symmetry.  An approximate (isotropic) 
 treatment of cell esds is used for estimating esds involving l.s. planes. 
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
I1 C8 2.064(3) . ?
O1 C11 1.205(6) . ?
O2 C11 1.336(6) . ?
O2 C12 1.442(5) . ?
O3 C13 1.203(5) . ?
O4 C13 1.313(5) . ?
O4 C14 1.442(5) . ?
O5 C5 1.356(5) . ?
O5 C7 1.429(7) . ?
N1 N2 1.359(5) . ?
N1 C1 1.450(7) . ?
N1 C8 1.343(8) . ?
N2 C10 1.319(5) . ?
C1 C2 1.375(7) . ?
C1 C6 1.373(6) . ?
C2 H2 0.9300 . ?
C2 C3 1.391(7) . ?
C3 H3 0.9300 . ?
C3 C4 1.358(7) . ?
C4 H4 0.9300 . ?
C4 C5 1.381(6) . ?
C5 C6 1.398(5) . ?
C6 H6 0.9300 . ?
C7 H7A 0.9600 . ?
C7 H7B 0.9600 . ?
C7 H7C 0.9600 . ?
C8 C9 1.406(8) . ?
C9 C10 1.415(7) . ?
C9 C11 1.466(8) . ?
C10 C13 1.501(5) . ?
C12 H12A 0.9600 . ?
C12 H12B 0.9600 . ?
C12 H12C 0.9600 . ?
C14 H14A 0.9600 . ?
C14 H14B 0.9600 . ?
C14 H14C 0.9600 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C11 O2 C12 116.2(4) . . ?
C13 O4 C14 116.0(3) . . ?
C5 O5 C7 118.1(4) . . ?
N2 N1 C1 118.1(4) . . ?
C8 N1 N2 112.2(4) . . ?
C8 N1 C1 129.5(4) . . ?
C10 N2 N1 104.9(4) . . ?
C2 C1 N1 118.2(5) . . ?
C6 C1 N1 118.1(4) . . ?
C6 C1 C2 123.4(5) . . ?
C1 C2 H2 121.5 . . ?
C1 C2 C3 116.9(4) . . ?
C3 C2 H2 121.5 . . ?
C2 C3 H3 119.3 . . ?
C4 C3 C2 121.4(5) . . ?
C4 C3 H3 119.3 . . ?
C3 C4 H4 119.7 . . ?
C3 C4 C5 120.7(4) . . ?
C5 C4 H4 119.7 . . ?
O5 C5 C4 116.5(4) . . ?
O5 C5 C6 124.0(4) . . ?
C4 C5 C6 119.6(4) . . ?
C1 C6 C5 118.0(4) . . ?
C1 C6 H6 121.0 . . ?
C5 C6 H6 121.0 . . ?
O5 C7 H7A 109.5 . . ?
O5 C7 H7B 109.5 . . ?
O5 C7 H7C 109.5 . . ?
H7A C7 H7B 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
N1 C8 I1 122.9(4) . . ?
N1 C8 C9 107.2(3) . . ?
C9 C8 I1 129.6(5) . . ?
C8 C9 C10 103.0(4) . . ?
C8 C9 C11 123.2(5) . . ?
C10 C9 C11 133.7(5) . . ?
N2 C10 C9 112.6(4) . . ?
N2 C10 C13 115.5(4) . . ?
C9 C10 C13 131.9(4) . . ?
O1 C11 O2 124.2(6) . . ?
O1 C11 C9 123.9(5) . . ?
O2 C11 C9 112.0(4) . . ?
O2 C12 H12A 109.5 . . ?
O2 C12 H12B 109.5 . . ?
O2 C12 H12C 109.5 . . ?
H12A C12 H12B 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
O3 C13 O4 124.7(4) . . ?
O3 C13 C10 121.9(4) . . ?
O4 C13 C10 113.4(3) . . ?
O4 C14 H14A 109.5 . . ?
O4 C14 H14B 109.5 . . ?
O4 C14 H14C 109.5 . . ?
H14A C14 H14B 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
I1 C8 C9 C10 -172.4(4) . . . . ?
I1 C8 C9 C11 4.0(8) . . . . ?
O5 C5 C6 C1 177.5(4) . . . . ?
N1 N2 C10 C9 1.8(5) . . . . ?
N1 N2 C10 C13 -179.2(4) . . . . ?
N1 C1 C2 C3 175.5(4) . . . . ?
N1 C1 C6 C5 -173.6(4) . . . . ?
N1 C8 C9 C10 2.0(6) . . . . ?
N1 C8 C9 C11 178.4(5) . . . . ?
N2 N1 C1 C2 -59.0(6) . . . . ?
N2 N1 C1 C6 115.9(5) . . . . ?
N2 N1 C8 I1 173.8(3) . . . . ?
N2 N1 C8 C9 -1.1(6) . . . . ?
N2 C10 C13 O3 23.0(6) . . . . ?
N2 C10 C13 O4 -154.0(4) . . . . ?
C1 N1 N2 C10 -177.4(4) . . . . ?
C1 N1 C8 I1 -9.6(8) . . . . ?
C1 N1 C8 C9 175.5(5) . . . . ?
C1 C2 C3 C4 -1.8(8) . . . . ?
C2 C1 C6 C5 1.0(7) . . . . ?
C2 C3 C4 C5 0.8(7) . . . . ?
C3 C4 C5 O5 -178.4(4) . . . . ?
C3 C4 C5 C6 1.2(7) . . . . ?
C4 C5 C6 C1 -2.0(6) . . . . ?
C6 C1 C2 C3 0.9(7) . . . . ?
C7 O5 C5 C4 178.4(4) . . . . ?
C7 O5 C5 C6 -1.2(6) . . . . ?
C8 N1 N2 C10 -0.4(5) . . . . ?
C8 N1 C1 C2 124.6(6) . . . . ?
C8 N1 C1 C6 -60.6(7) . . . . ?
C8 C9 C10 N2 -2.4(6) . . . . ?
C8 C9 C10 C13 178.8(5) . . . . ?
C8 C9 C11 O1 32.7(8) . . . . ?
C8 C9 C11 O2 -147.5(5) . . . . ?
C9 C10 C13 O3 -158.3(5) . . . . ?
C9 C10 C13 O4 24.8(7) . . . . ?
C10 C9 C11 O1 -152.2(5) . . . . ?
C10 C9 C11 O2 27.6(8) . . . . ?
C11 C9 C10 N2 -178.3(5) . . . . ?
C11 C9 C10 C13 3.0(9) . . . . ?
C12 O2 C11 O1 -2.3(7) . . . . ?
C12 O2 C11 C9 178.0(4) . . . . ?
C14 O4 C13 O3 6.4(7) . . . . ?
C14 O4 C13 C10 -176.8(4) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.271
_oxdiff_exptl_absorpt_empirical_full_min 0.838
